EP0492367B1 - Mélanges d'herbicides et d'antidotes - Google Patents

Mélanges d'herbicides et d'antidotes Download PDF

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Publication number
EP0492367B1
EP0492367B1 EP91121623A EP91121623A EP0492367B1 EP 0492367 B1 EP0492367 B1 EP 0492367B1 EP 91121623 A EP91121623 A EP 91121623A EP 91121623 A EP91121623 A EP 91121623A EP 0492367 B1 EP0492367 B1 EP 0492367B1
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Prior art keywords
alkyl
alkoxy
carbonyl
phenyl
halogen
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EP91121623A
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German (de)
English (en)
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EP0492367A2 (fr
EP0492367A3 (en
Inventor
Klaus Dr. Bauer
Hermann Dr. Bieringer
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Bayer CropScience AG
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Aventis CropScience GmbH
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the invention relates to the technical field of crop protection agents, in particular Active ingredient-antidote combinations that are excellent for use against Harmful plants in crops are suitable.
  • Some newer herbicidal agents have very good efficacies and Selectivities and can fight a wide range of different weeds and / or grasses in special crops such as soybean or corn or cereals are used. Other crops, however, are affected by this Herbicides damaged, so that use in such crops is not possible or only in small amounts that are not the optimal broad herbicides Ensure effectiveness.
  • Such herbicides are, for example some herbicides from the group of sulfonylureas and imidazolinones.
  • Herbicides of these two structural groups are related insofar as they are in the plant partially block the same biosynthetic pathways in the metabolism. Both Herbicide classes primarily inhibit the enzyme acetolactate synthase (ALS), too Acetohydroxy acid synthase (AHAS), an important key enzyme called in the biosynthesis of the branched chain amino acids valine, leucine and isoleucine plays an important role (see e.g. Dale L.
  • imidazolinones and sulfonylureas have other properties such as application rate, soil effectiveness etc. are very different, so that a Equivalence is not given, the herbicides from these classes of substances
  • the reason for the partially similar mechanism of action in the plant Metabolism have common properties.
  • many herbicides of the substance classes mentioned are not selective in cereal crops and / or not used in maize, because these crops at least in the desired dosages that are used for broad herbicidal activity Weeds and grasses are required to be damaged.
  • EP-A-94349 discloses safeners from the quinoline-8-oxyalkanecarboxylic acid series, especially for use with aryloxy and heteroaryloxy-phenoxycarboxylic acid herbicides be recommended.
  • Sulfonylureas are among them in a variety of structurally different herbicides as possible herbicides for combination with mentioned the safenem; two examples, wheat seeds with a Quinoline oxyacetic acid methyl pickled and the acreage with a Treated sulfonylurea in the post-emergence process or in the pre-emergence process are also mentioned.
  • the safener effect of the well-known sulfonylurea safener combination is not sufficient, especially not for the Use of the safener and the herbicide in the post-emergence process in cereals, such as Wheat or barley, or in corn.
  • EP-A-333131 relates to phenylpyrazole carboxylic acid derivatives which are used as safeners in Combination with herbicides of the phenoxyphenoxycarboxylic acid ester type, Chloroacetanilides, thiocarbamates and dimedone derivatives are described. A The safener effect for sulfonylureas or imidazolinones is not mentioned there.
  • EP-A-0147365 relates to selective herbicidal compositions which contain a substituted N-phenyl-N'-pyrimidinyl (or -triazinyl) -sulfonylurea herbicide and a safener from the Group consisting of cyanomethoxyimino-benzacetonitri, N, N-diallyldichloroacetamide, 2-chloro-5-benzyloxycarbonyl-3-trifluoromethylthiazole, 1,8-naphthalenedicarboxylic acid anhydride and 3-N-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine contain.
  • crops such as. B. wheat and barley and corn can be protected from undesirable damage to the above-mentioned herbicides when applied together with certain compounds which act as herbicidal antidotes or safeners.
  • imidazolinones and certain safeners from the quinoline-8-oxyalkanecarboxylic acid series are particularly suitable for the selective control of harmful plants in maize crops using the post-emergence method.
  • alkyl, alkenyl and alkynyl are straight-chain or branched; the same applies to substituted alkyl, alkenyl and alkynyl radicals such as haloalkyl, hydroxyalkyl, alkoxycarbonyl, etc .; Alkyl means e.g. B.
  • Alkenyl means e.g. B. Allyl, 1-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methyl-but-3-ene and 1-methyl- but-2-ene; Alkynyl means e.g. B.
  • Halogen means fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, especially fluorine or chlorine;
  • Haloalkyl, alkenyl and alkynyl are alkyl, alkenyl and alkynyl, for example, substituted by halogen.
  • B. CF 3 , CHF 2 , CH 2 F, CF 3 CF 2 , CH 2 FCHCl, CCl 3 , CHCl 2 , CH 2 CH 2 Cl; Haloalkoxy is e.g. B.
  • phenyl is phenyl or substituted phenyl; substituted phenyl is phenyl which is monosubstituted or polysubstituted by radicals from the group halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 -haloalkoxy and nitro is substituted, e.g. B.
  • the compounds of the formula B1 are known from WO-91/08202 (Internationale Patent application PCT / EP 90/01966) and literature cited there known or can be produced by or analogously to the processes described there.
  • the herbicidal active ingredients and the safeners mentioned can be taken together (as finished Formulation or in the tank mix method) or in any order are applied one after the other.
  • the weight ratio safener: herbicide can vary within wide limits and is preferably in the range from 1:10 to 10: 1, especially from 1:10 to 5: 1.
  • the optimal amounts of herbicide and Safeners are of the type of herbicide used or of the safener used and depending on the type of crop to be treated and leave determine yourself on a case-by-case basis by means of appropriate preliminary tests.
  • the main areas of application for the application of safeners are above all Grain crops (wheat, rye, barley, oats), rice, corn, sorghum, but also Cotton and soybeans, preferably cereals and corn.
  • Type B safeners can be used to pretreat the Seeds of the crop (dressing the seeds) are used or before Seed introduced into the furrows or together with the herbicide before or be applied after emergence of the plants.
  • Pre-emergence treatment includes both the treatment of the acreage before sowing and the Treatment of the sown but not overgrown areas.
  • Co-application with the herbicide is preferred in Post-emergence procedure. For this purpose tank mixes or ready formulations be used.
  • the method with the combined use of herbicide and safener in the post-emergence process represents a significant practical advantage.
  • the farmer saves substantial costs by one step of the common application and, above all, does not have to Carry out labor-intensive seed dressing, which requires a special dressing device.
  • the work involved in the additional application of the safener is practically negligible, especially when herbicide and safener are used and applied as a finished formulation.
  • the required application rates of the safener can vary depending on the indication and Herbicide used fluctuate within wide limits and are usually in the range of 0.001 to 5 kg, preferably 0.005 to 0.5 kg of active ingredient per hectare.
  • the present invention therefore also relates to a method for protection of crops before phytotoxic side effects of herbicides mentioned type A), which is characterized in that an effective amount a connection of the formulas mentioned (B1) before, after or simultaneously with the Herbicide of the type A) mentioned, preferably together with the herbicide Type A) post-emergence, on the plants, plant seeds or the Cultivation area is applied.
  • the herbicides mentioned can be formulated in different ways, depending on according to which biological and / or chemical-physical parameters are specified.
  • Examples of possible formulations are: Wettable powders (WP), emulsifiable concentrates (EC), water-soluble powders (SP), water-soluble concentrates (SL), concentrated emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions, Capsule suspensions (CS) oil or water-based dispersions (SC), Suspo emulsions, suspension concentrates, dusts (DP), oil-miscible Solutions (OL), pickling agents, granules (GR) in the form of micro, spray, elevator and Adsorption granules, granules for soil or litter application, water-soluble granules (SG), water-dispersible granules (WG), ULV formulations, Microcapsules and waxes
  • combinations with others can also be made pesticidal substances, fertilizers and / or growth regulators manufacture, e.g. in the form of a finished formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water Active substance in addition to a diluent or inert substance or wetting agent, e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols and fatty amines, Fatty alcohol polyglycol ether sulfates, alkanesulfonates or alkylarylsulfonates and Dispersants, e.g. sodium lignosulfonic acid, 2,2, -dinaphthylmethane-6,6'-disulfonic acid Sodium, sodium dibutylnaphthalenesulfonic acid or also Contain oleylmethyl tauric acid sodium.
  • a diluent or inert substance or wetting agent e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols and fatty amines, Fatty alcohol polyglycol ether sulf
  • Emulsifiable concentrates are made by dissolving the active ingredient in one organic solvents, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers.
  • emulsifiers for example: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as Fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, Propylene oxide-ethylene oxide condensation products (e.g. block polymers), Alkyl polyether, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester or Polyoxethylene sorbitol ester.
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate
  • Dusts are obtained by grinding the active ingredient with finely divided solid Fabrics, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or Diatomaceous earth.
  • finely divided solid Fabrics e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or Diatomaceous earth.
  • Granules can either by spraying the active ingredient adsorbable, granulated inert material or by Application of active ingredient concentrates using adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of Carriers such as sand, kaolinite or granulated inert material. Can too suitable active ingredients in the usual for the production of fertilizer granules Way - if desired in a mixture with fertilizers - granulated.
  • adhesives e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils
  • the agrochemical preparations usually contain 0.1 to 99 Weight percent, in particular 0.1 to 95 wt .-%, active ingredients of type B) or Antidote / herbicide active ingredient mixture A) and B) and 1 to 99.9% by weight, in particular 5 to 99.8% by weight of a solid or liquid additive and 0 to 25% by weight, in particular 0.1 to 25% by weight of a surfactant.
  • the active ingredient concentration in wettable powders is, for example, about 10 to 90% by weight, the remainder to 100% by weight consists of customary formulation components.
  • the active substance concentration is approximately 1 to 80% by weight of active substances.
  • Dust-like formulations contain about 1 to 20% by weight of active ingredients, sprayable solutions about 0.2 to 20% by weight of active ingredients.
  • the active ingredient content depends in part on whether the active compound is in liquid or solid form. As a rule, the content of the water-dispersible granules is between 10 and 90% by weight.
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers.
  • the formulations available in commercial form are used optionally diluted in a conventional manner, e.g. with wettable powders, emulsifiable Concentrates, dispersions and water-dispersible granules using water. Dust-like preparations, granules and sprayable solutions are available usually no longer diluted with other inert substances.
  • Particularly good efficacies of the agents according to the invention can be achieved if, in addition to the surfactants contained in the formulations further wetting agents in concentrations of 0.1 to 0.5% by weight in the tank mix process be added, e.g. B. non-ionic wetting agents or wetting agents of the type the fatty alcohol polyol ether sulfates (see e.g. German patent application P 4029304.1). With the external conditions such as temperature, humidity, the type of the herbicide used, among others the required application rate varies "Safener".
  • the crops, weeds and grasses were grown in the field or in Greenhouse grown in plastic pots up to the 4- to 5-leaf stage and then according to the invention with compounds of types A) and B) in Treated post-emergence.
  • the compounds of type A) and B) were thereby in the form of aqueous suspensions or emulsions with a Water application rate equivalent to 300 l / ha applied. 4 weeks after the Treatment was done visually for any type of damage caused by the plants applied herbicides rated, in particular the extent of continued growth inhibition was taken into account. The evaluation took place in Percentages compared to untreated controls.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Claims (10)

  1. Agents herbicides, caractérisés en ce qu'ils contiennent
    A) un ou plusieurs herbicides pris dans le groupe constitué par les sulfonylurées et les imidazolinones et
    B) un ou plusieurs composés de formule B1
    Figure 00340001
    où
    X
    représente un atome d'hydrogène, un atome d'halogène, des groupes alkyle en C1-C4, alkoxy C1-C4, nitro ou halogénoalkyle en C1-C4,
    Z
    représente des groupes OR1 ou SR1,
    R1
    représente un atome d'hydrogène, des groupes alkyle en C1-C18, cycloalkyle en C3-C12, alcényle en C2-C8 ou alcynyle en C2-C8,
    où chacun des restes carbonés précités pouvant être, indépendamment les uns des autres, non substitué ou substitué une ou plusieurs fois par des restes pris dans le groupe constitué par des atomes d'hydrogène, des groupes hydroxy, alkoxy en C1-C8, (alkyl en C1-C8)thio, (alcényl en C2-C8)thio, (alcynyl en C2-C8)thio, alcényloxy en C2-C8, alcynyloxy en C2-C8, cycloalkyle en C3-C7, cycloalkoxy en C3-C7, cyano, mono- et di(alkyl en C1-C4)amino, (alkoxy en C1-C8)carbonyle, (alcényloxy en C2-C8)carbonyle, (alkyl en C1-C8)thiocarbonyle, (alcynyloxy en C2-C8)carbonyle, (alkyl an C1-C8)carbonyle, (alcényl en C2-C8)carbonyle, (alcynyl en C2-C8)carbonyle, 1-(hydroxyimino)-alkyle en C1-C6, 1-(alkylimino en C1-C4)-alkyle en C1-C6, 1-(alkoxyimino en C1-C4)alkyle en C1-C6, (alkyl en C1-C8)carbonylamino, (alcényl en C2-C8)carbonylamino, (alcynyl en C2-C8)carbonylamino, aminocarbonyle, (alkyl en C1-C8)aminocarbonyle, di-(alkyl en C1-C6)aminocarbonyle, (alcényl an C2-C6)aminocarbonyle, (alcynyl en C2-C6)aminocarbonyle, (alkoxy en C1-C8)-carbonylamino, (alkyl en C1-C8)-aminocarbonylamino, (alkyl en C1-C6)-carbonyloxy, lequel est non substitué ou substitué par des atomes d'halogènes, des groupes NO2, alkoxy an C1-C4 ou par un groupe phényle éventuellement substitué, (alcényl en C2-C6)-carbonyloxy, (alcynyl en C2-C6)-carbonyloxy, (alkyl en C1-C8)sulfonyle, phényle, phénylalkoxy en C1-C6, phényl(alkoxy en C1-C6)carbonyle, phénoxy, phénoxyalkoxy en C1-C6, phénoxy(alkoxy en C1-C6)carbonyle, phénylcarbonyloxy, phénylcarbonylamino, phényl(alkyl en C1-C6)carbonylamino, les 9 derniers restes cités sont non substitués ou susbtitués dans le cycle phényle une ou plusieurs fois par des restes pris dans le groupe constitué par des atomes d'halogènes, des groupes alkyle an C1-C4, alkoxy C1-C4, halogénoalkyle en C1-C4, halogénoalkoxy en C1-C4 et nitro, et des restes dans les formules -SiR ' / 3 , -O-SiR ' / 3, (R')3Si-alkoxy en C1-C6, -CO-O-NR ' / 2 , -O-N=CR ' / 2, -N=CR ' / 2, -O-NR ' / 2, -CH(OR')2 et -O-(CH2)m-CH(OR')2, où R' dans les formules précitées représentent, indépendamment les un des autres, des atomes d'hydrogène, des groupes alkyle en C1-C4 ou phényle, lequel est non substitué ou substitué une ou plusieurs fois par des restes pris dans le groupe constitué par des atomes d'halogènes, des groupes alkyle en C1-C4, alkoxy C1-C4, halogénoalkyle en C1-C4, halogénoalkoxy en C1-C4 et nitro, ou par paires, représentent une chaíne alkylène en C2-C6 et m = 0 à 6, et un reste alkoxy de formule R''O-CHR'''(OR'')-alkoxy en C1-C6, où R'' représentent, indépendamment les uns des autres, des groupes alkyle en C1-C4 ou conjointement un groupe alkylène en C1-C6 et R''' représente un atome d'hydrogène ou un groupe alkyle en C1-C4,
    n
    est un entier de 1 à 5 et
    W
    représente un reste hétérocyclique bivalent à 5 chaínons de formule W4
    Figure 00360001
    en une quantité efficace.
  2. Agents selon la revendication 1, caractérisés en ce que
    R1
    représente un atome d'hydrogène, des groupes alkyle en C1-C12, cycloalkyle en C3-C7, alcényle en C2-C8 ou alcynyle en C2-C8,
    où chacun des restes carbonés précités, indépendamment les uns des autres, est non substitué ou substitué une ou plusieurs fois par des atomes d'halogènes ou une ou deux fois, de préférence jusqu'à une fois par des restes pris dans le groupe constitué par des restes hydroxy, alkoxy en C1-C4, (alkyl en C1-C4)thio, alcényloxy en C2-C4, alcynyloxy en C2-C4, mono- et di(alkyl en C1-C2)amino, (alkoxy en C1-C4)-carbonyle, (alcényloxy en C2-C4)carbonyle, (alcynyloxy en C2-C4)carbonyle, (alkyl en C1-C4)-carbonyle, (alcényl en C2-C4)carbonyle, (alcynyl en C2-C4)carbonyle, 1-(hydroxyimino)-alkyle en C1-C4, 1-(alkylimino en C1-C4)-alkyle en C1-C4, 1-(alkoxyimino en C1-C4)-alkyle en C1-C4, (alkyl en C1-C4)-sulfonyle, phényle, phénylalkoxy en C1-C4, phényl(alkoxy en C1-C4)carbonyle, phénoxy, phénoxyalkoxy en C1-C4, phénoxy(alkoxy en C1-C4)carbonyle, les 6 derniers restes cités sont non substitués ou susbtitués dans le cycle phényle ou substitués une ou plusieurs fois par des restes pris dans le groupe constitué par des atomes d'halogènes, des groupes alkyle en C1-C2, alkoxy C1-C2, halogénoalkyle en C1-C2, halogénoalkoxy en C1-C2 et nitro, et des restes dans les formules -SiR ' / 3 , -O-N=CR ' / 2, -N=CR ' / 2 et -O-NR ' / 2, où R' dans les formules précitées représentent, indépendamment les un des autres, des atomes d'hydrogène, des groupes alkyle en C1-C2 ou phényle, lequel est non substitué ou substitué une ou plusieurs fois par des restes pris dans le groupe constitué par des atomes d'halogènes, des groupes alkyle en C1-C2, alkoxy C1-C2, halogénoalkyle en C1-C2, halogénoalkoxy en C1-C2 et nitro, ou par paires, représentent une chaíne alkylène en C4-C5.
  3. Agents selon la revendication 1 ou 2, caractérisés en ce que
    X
    représente un atome d'hydrogène, un atome d'halogène, des groupes nitro ou halogénoalkyle en C1-C4,
    n
    va de 1 à 3,
    Z
    représente un reste de formule OR1,
    R1
    représente un atome d'hydrogène, des groupes alkyle en C1-C8 ou cycloalkyle en C3-C7,
    où chacun des restes carbonés précités est, indépendamment les uns des autres, non substitué ou substitué une ou plusieurs fois par des restes pris dans le groupe constitué par des atomes d'halogènes, ou substitué une ou deux fois, de préférence est non substitué ou substitué une fois par des restes pris dans le groupe constitué par des groupes hydroxy, alkoxy en C1-C4, (alkoxy en C1-C4)carbonyle, (alcényloxy en C2-C6)carbonyle, (alcynyloxy en C2-C6)-carbonyle, 1-(hydroxyimino)alkyle en C1-C4, 1-(alkylimino en C1-C4)-alkyle en C1-C4, 1-(alkoxyimino en C1-C4)-alkyle en C1-C4 et des restes de formules -SiR ' / 3 , -O-N=CR ' / 2, -N=CR ' / 2 et -O-NR ' / 2 , où R' dans les formules précitées représentent, indépendamment les un des autres, des atomes d'hydrogène ou des groupes alkyle en C1-C4 ou par paires, représentent une chaíne alkylène en C4-C5.
  4. Agents selon l'une des revendications 1 à 3, caractérisés en ce que
    X
    représente un atome d'hydrogène, un atome d'halogène, des groupes nitro, alkyle en C1-C4, halogénoalkyle en C1-C2,
    n
    va de 1 à 3,
    Z
    représente un reste de formule OR1,
    R1
    représente un atome d'hydrogène, des groupes alkyle en C1-C4 ou (alkoxy en C1-C4)carbonylalkyle en C1-C4.
  5. Agents selon l'une des revendications 1 à 4, caractérisés en ce qu'ils contiennent un ou plusieurs herbicides pris dans le groupe constitué par des phénylsulfonylurées, des thiénylsulfonylurées, des pyrazolsulfonylurées, des dérivés de sulfone diamide, des pyridylsulfonylurées, des phénoxysulfonylurées et des imidazolinones.
  6. Agents selon l'une des revendications 1 à 5, caractérisés en ce qu'ils contiennent un ou plusieurs herbicides pris dans le groupe comportant chlorimunoethyl, nicosulfuron, DPX-E 9636, amidosulfuron, thiameturon-methyl, primisulfuron, pyridylsulfonylurées de formule A1 ou leurs sels
    Figure 00380001
    où
    E
    représente CH ou N,
    R4
    représente un atome d' iode ou un groupe NR9R10,
    R5
    représente un atome d' hydrogène, un atome d'halogène, des groupes cyano, alkyle en C1-C3, alkoxy en C1-C3, haloalkyle en C1-C3, haloalkoxy en C1-C3, (alkyl en C1-C3)thio, (alkoxy en C1-C3)-alkyle en C1-C3, (alkoxy en C1-C3)-carbonyle, mono- ou di-(alkyl en C1-C3)-amino, (alkyl en C1-C3)sulfinyle ou -sulfonyle, SO2-NRaRb ou CO-NRaRb,
    Ra, Rb
    représentent, indépendamment l'un de l'autre, un atome d'hydrogène, des groupes alkyle en C1-C3, alcényle en C1-C3, alcynyle en C1-C3 ou conjointement représentent -(CH2)4-, -(CH2)5- ou -(CH2)2-O-(CH2)2-,
    R6
    représente un atome d'hydrogène ou CH3,
    R7
    représente un atome d'halogène, des groupes alkyle en C1-C2, alkoxy en C1-C2, haloalkyle en C1-C2, haloalkoxy en C1-C2 ou OCH2CF3,
    R8
    représente des groupes alkyle en C1-C2, haloalkoxy en C1-C2 ou alkoxy en C1-C2, et
    R9
    représente un groupe alkyle en C1-C4 et
    R10
    représente un groupe (alkyl en C1-C4)sulfonyle ou
    R9 et R10
    forment ensemble une chaíne de formule -(CH2)3SO2- ou -(CH2)4-SO2-,
    alkoxyphénoxysulfonylurées de formule A2 ou leurs sels
    Figure 00390001
    où
    E
    représente CH ou N,
    R11
    représente des groupes éthoxy, propoxy ou isopropoxy,
    R12
    représente un atome d'hydrogène, un atome d'halogène, des groupes NO2, CF3, CN, alkyle en C1-C4, alkoxy en C1-C4, (alkyl en C1-C4)thio ou (alkoxy en C1-C3)-carbonyle,
    n
    vaut 1, 2 ou 3,
    R13
    représente un atome d' hydrogène, un groupe alkyle en C1-C4 ou alcényle en C3-C4,
    R14, R15
    représentent, indépendamment l'un de l'autre, un atome d'halogène, des groupes alkyle en C1-C2, alkoxy en C1-C2, haloalkyle en C1-C2, haloalkoxy en C1-C2 ou (alkoxy on C1-C2)-alkyle en C1-C2,
    3-(4-éthyl-6-méthoxy-1,3,5-triazin-2-yl)-1-(2,3-dihydro-1,1-dioxo-2-méthylbenzo[b]thiophén-7-sulfonyl)-urée,
    3-(4-éthoxy-6-éthyl-1,3,5-triazin-2-yl)-1-(2,3-dihydro-1,1-dioxo-2-méthylbenzo[b]thiophén-7-sulfonyl)-urée,
    imazethapyr, imazaquin et imazethamethabenz.
  7. Agents selon l'une des revendications 1 à 6, caractérisés en ce que le rapport pondéral antidote:herbicide se trouve dans le domaine de 1:10 à 10:1.
  8. Agents selon l'une des revendications 1 à 7, caractérisés en ce qu'il contiennent de 0,1 à 99% massiques de substances actives du type B) ou du mélange antidote/substance active herbicide A) et B) et de 1 à 99,9% massiques d'une matière d'addition solide ou liquide et de 0 à 25% massiques d'une agent de surface.
  9. Procédé pour la protection de cultures végétales contre les effets secondaires phytotoxiques des herbicides du type A), tels que définis aux revendications 1, 5 et 6, caractérisé en ce qu'on applique une quantité efficace d'un ou plusieurs composés de formule (B1), tels que définis aux revendications 1 à 4, avant, après ou on même temps que l'herbicide du type A), sur les plantes, la semence des plantes ou la surface cultivable.
  10. Procédé selon la revendication 9, caractérisé en ce que les cultures végétales sont les céréales ou le maïs.
EP91121623A 1990-12-21 1991-12-17 Mélanges d'herbicides et d'antidotes Expired - Lifetime EP0492367B1 (fr)

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CA2085148A1 (fr) * 1991-12-14 1993-06-15 Hermann Bieringer Combinaison d'inhibiteurs de l'als, d'insecticides et de phytoprotecteurs, procedes pour leur obtention, et leur utilisation comme agents phytoprotecteurs
EP0558448A1 (fr) * 1992-02-26 1993-09-01 Ciba-Geigy Ag Dérivés de 1,5-diphénylpyrazole-3-acide carboxylique comme antidotes pour les herbicides de sulfonylurée
DE59309481D1 (de) * 1992-05-15 1999-05-06 Hoechst Schering Agrevo Gmbh Synergistisch wirksame Herbizidkombinationen
EP0671880A1 (fr) * 1992-07-08 1995-09-20 Ciba-Geigy Ag Composition herbicide selective
US5541148A (en) * 1992-07-08 1996-07-30 Ciba-Geigy Corporation Selective safened herbicidal composition comprising 2-ethoxycarbonyl-3-(4,6-dimethoxypyrimidine-2-yl) oxy-pyridine and an acylsulfamoylphenyl-urea safener
FI93687C (fi) * 1992-07-29 1995-05-26 Novasso Oy Menetelmä siementen päällystämiseksi
MY109136A (en) * 1992-07-30 1996-12-31 Ciba Geigy Ag Selective herbicidal composition
TW225979B (fr) * 1992-07-30 1994-07-01 Ciba Geigy Ag
EP0597807A1 (fr) * 1992-11-12 1994-05-18 Ciba-Geigy Ag Agent selectivement herbicide
EP0600836B1 (fr) * 1992-12-02 1998-08-05 Novartis AG Agent selectivement herbicide
EP0612473A1 (fr) * 1993-02-26 1994-08-31 Monsanto Europe S.A./N.V. Combinaisons herbicides comprenant un dérivé de triazole et un herbicide de sulfonylurée
DE4333249A1 (de) * 1993-09-30 1995-04-06 Hoechst Schering Agrevo Gmbh Neue Mischungen aus Herbiziden und Antidots
EE9400262A (et) * 1993-12-08 1996-02-15 Ciba-Geigy Ag Selektiivne herbitsiidsegu ja selle kasutamise meetod
DE4440354A1 (de) * 1994-11-11 1996-05-15 Hoechst Schering Agrevo Gmbh Kombinationen aus Phenylsulfonylharnstoff-Herbiziden und Safenern
US5696024A (en) * 1995-06-06 1997-12-09 American Cyanmid Herbicidal water soluble granular compositions
CN1202800A (zh) * 1995-11-23 1998-12-23 诺瓦提斯公司 除草组合物
US7071146B1 (en) 1996-11-11 2006-07-04 Syngenta Crop Protection, Inc. Herbicidal composition
US5870190A (en) * 1997-11-25 1999-02-09 Venturedyne, Ltd. Particle sensor and related method offering improved particle discrimination
AU3982699A (en) * 1998-05-14 1999-11-29 E.I. Du Pont De Nemours And Company Crop-safened herbicidal mixtures
DE19836700A1 (de) * 1998-08-13 2000-02-17 Hoechst Schering Agrevo Gmbh Herbizide Mittel für tolerante oder resistente Getreidekulturen
US20040048748A1 (en) * 2002-09-10 2004-03-11 Herb Friend Pesticide-free weed and grass killer
EA012521B1 (ru) * 2003-11-03 2009-10-30 Байер Кропсайенс Аг Жидкий препарат, его применение, способ его получения и способ борьбы с сорными растениями
ATE442044T1 (de) * 2004-03-27 2009-09-15 Bayer Cropscience Ag Herbizid-safener-kombination
HUE025200T2 (en) * 2006-07-26 2016-02-29 Dow Agrosciences Llc Herbicidal preparations
EP2052616A1 (fr) * 2007-10-24 2009-04-29 Bayer CropScience AG Combinaison d'herbicide et de phytoprotecteurs

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CA2058284C (fr) 1999-12-07
ZA919983B (en) 1992-09-30
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JP3362863B2 (ja) 2003-01-07
ES2151879T3 (es) 2001-01-16
EP1008297B1 (fr) 2003-03-19
ATE196591T1 (de) 2000-10-15
EP1008297A2 (fr) 2000-06-14
EP1008297A3 (fr) 2000-08-02
HU914074D0 (en) 1992-03-30
DE59109197D1 (de) 2000-11-02
IL100426A0 (en) 1992-09-06
AU8989791A (en) 1992-06-25
MX9102750A (es) 1992-06-01
ES2194629T3 (es) 2003-12-01
BR9105496A (pt) 1992-09-01
DE59109249D1 (de) 2003-04-24
AU644503B2 (en) 1993-12-09
KR920011358A (ko) 1992-07-24
ATE234559T1 (de) 2003-04-15
HU211899B (en) 1996-01-29
JPH04308508A (ja) 1992-10-30
EP0492367A2 (fr) 1992-07-01
EP0492367A3 (en) 1993-01-20
HUT59559A (en) 1992-06-29

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